icariside B5

Details

• Internal ID: c07fbc14-2cbf-4964-bc02-a2138efbc74f
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
• IUPAC Name: (4S)-4-hydroxy-3,5,5-trimethyl-4-[(3R)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl]cyclohex-2-en-1-one
• SMILES (Canonical): CC1=CC(=O)CC(C1(CCC(C)OC2C(C(C(C(O2)CO)O)O)O)O)(C)C
• SMILES (Isomeric): CC1=CC(=O)CC([C@]1(CC[C@@H](C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)(C)C
• InChI: InChI=1S/C19H32O8/c1-10-7-12(21)8-18(3,4)19(10,25)6-5-11(2)26-17-16(24)15(23)14(22)13(9-20)27-17/h7,11,13-17,20,22-25H,5-6,8-9H2,1-4H3/t11-,13-,14-,15+,16-,17-,19-/m1/s1
• InChI Key: CZYPGTRKJFYXLT-SUHXYMONSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₃₂O₈
• Molecular Weight: 388.50 g/mol
• Exact Mass: 388.20971797 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -0.35
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

• 114226-08-3
• CHEMBL3326713
• CHEBI:181563
• AKOS040763300
• NCGC00385777-01
• (4S)-4-hydroxy-3,5,5-trimethyl-4-[(3R)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl]cyclohex-2-en-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6938	69.38%
Caco-2	-	0.7582	75.82%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8903	89.03%
OATP2B1 inhibitior	-	0.8600	86.00%
OATP1B1 inhibitior	+	0.8851	88.51%
OATP1B3 inhibitior	-	0.2467	24.67%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5818	58.18%
BSEP inhibitior	-	0.8338	83.38%
P-glycoprotein inhibitior	-	0.8060	80.60%
P-glycoprotein substrate	-	0.8023	80.23%
CYP3A4 substrate	+	0.6466	64.66%
CYP2C9 substrate	-	0.8054	80.54%
CYP2D6 substrate	-	0.8858	88.58%
CYP3A4 inhibition	-	0.8724	87.24%
CYP2C9 inhibition	-	0.7739	77.39%
CYP2C19 inhibition	-	0.8237	82.37%
CYP2D6 inhibition	-	0.9329	93.29%
CYP1A2 inhibition	-	0.8449	84.49%
CYP2C8 inhibition	-	0.9337	93.37%
CYP inhibitory promiscuity	-	0.9355	93.55%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7327	73.27%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9797	97.97%
Skin irritation	-	0.6440	64.40%
Skin corrosion	-	0.9605	96.05%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6764	67.64%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.7782	77.82%
skin sensitisation	-	0.8474	84.74%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.6961	69.61%
Estrogen receptor binding	-	0.5103	51.03%
Androgen receptor binding	+	0.5570	55.70%
Thyroid receptor binding	+	0.6697	66.97%
Glucocorticoid receptor binding	+	0.5683	56.83%
Aromatase binding	+	0.6371	63.71%
PPAR gamma	-	0.4853	48.53%
Honey bee toxicity	-	0.8331	83.31%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6850	68.50%
Fish aquatic toxicity	+	0.9487	94.87%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.68%	91.11%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	96.77%	83.57%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.69%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.58%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.45%	98.95%
CHEMBL220	P22303	Acetylcholinesterase	90.95%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.75%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	86.82%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.01%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.50%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.27%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.46%	96.47%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.40%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.32%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.63%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.53%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.53%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.39%	96.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.08%	93.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.78%	99.23%
CHEMBL1937	Q92769	Histone deacetylase 2	80.49%	94.75%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.21%	96.21%

Plants that contains it

• Abies spectabilis
• Alcea rosea
• Alpinia roxburghii
• Antidesma membranaceum
• Balanops australiana
• Bobgunnia madagascariensis
• Calodendrum capense
• Camellia sinensis
• Campanula medium
• Casearia sylvestris
• Croton caudatus
• Davallia perdurans
• Elaeocarpus fuscoides
• Euonymus tingens
• Euphorbia cornigera
• Glochidion zeylanicum
• Gonzalezia decurrens
• Hylocomium splendens
• Jacobaea adonidifolia
• Kokoona reflexa
• Macaranga tanarius
• Maesa ramentacea
• Meconopsis horridula
• Mentha spicata subsp. spicata
• Millettia laurentii
• Monodora tenuifolia
• Ocimum tenuiflorum
• Oxera splendida
• Pinus strobus
• Pinus sylvestris
• Piper retrofractum
• Pluchea odorata
• Salacia lehmbachii
• Salvia yosgadensis
• Sideritis brevibracteata
• Sideroxylon cubense
• Stevia eupatoria
• Trachelospermum jasminoides
• Vitex pinnata

Cross-Links

• PubChem: 14135399
• NPASS: NPC223834
• LOTUS: LTS0154767
• wikiData: Q104665543